(E)-5-((2,3-dichloro-5-ethoxy-6-hydroxybenzylidene)amino)-1H-benzo[d]imidazol-2(3H)-one

ID: ALA3335246

PubChem CID: 136044165

Max Phase: Preclinical

Molecular Formula: C16H13Cl2N3O3

Molecular Weight: 366.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc(Cl)c(Cl)c(/C=N/c2ccc3[nH]c(=O)[nH]c3c2)c1O

Standard InChI:  InChI=1S/C16H13Cl2N3O3/c1-2-24-13-6-10(17)14(18)9(15(13)22)7-19-8-3-4-11-12(5-8)21-16(23)20-11/h3-7,22H,2H2,1H3,(H2,20,21,23)/b19-7+

Standard InChI Key:  UOUNOYWIBROXIZ-FBCYGCLPSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.4106   -4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4094   -5.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1175   -5.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8272   -5.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8243   -4.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1157   -3.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5305   -3.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2397   -4.3122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9459   -3.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6536   -4.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6424   -2.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9396   -3.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3566   -3.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3586   -3.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1343   -4.1465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6118   -3.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1310   -2.8280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4289   -3.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5355   -5.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1173   -6.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8249   -6.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247   -7.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028   -3.9127    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -3.0951    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 14  1  0
 13 11  1  0
 11 12  2  0
 12  9  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 16 18  2  0
  4 19  1  0
  3 20  1  0
 20 21  1  0
 21 22  1  0
  1 23  1  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335246

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 366.20

Molecular Weight (Monoisotopic): 365.0334

AlogP: 4.02

#Rotatable Bonds: 4

Polar Surface Area: 90.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.30

CX Basic pKa: 0.62

CX LogP: 4.12

CX LogD: 4.07

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -1.06

References

1. Shim HJ, Yang HR, Kim HIe, Kang SA, No KT, Jung YH, Lee ST..  (2014)  Discovery of (E)-5-(benzylideneamino)-1H-benzo[d]imidazol-2(3H)-one derivatives as inhibitors for PTK6.,  24  (19): [PMID:25205190] [10.1016/j.bmcl.2014.08.036]

Source

Source(1):

• Scientific Literature